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Hydrochloric Acid → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-amino-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 2353878
Notes
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Reaction equation

HRID 2353878 reaction equation
Cl.[C:2]([N:5]([CH2:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=1)[CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:8]2[CH:19]=[C:20]([N:23]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=[CH:22][C:7]1=2)(=[O:4])[CH3:3]>O1CCCC1.C(OCC)(=O)C>[C:2]([N:5]([CH2:37][C:38]1[CH:39]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:41]=[C:42]([C:44]([F:47])([F:45])[F:46])[CH:43]=1)[CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:8]2[CH:19]=[C:20]([NH2:23])[CH:21]=[CH:22][C:7]1=2)(=[O:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86616066Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-(benzhydrylideneamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Product 1

HCID 59003104Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-amino-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Add 2 N hydrochloric acid (0.19 mL) to a solution of isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-(benzhydrylideneamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.520 g, 0.747 mmol) in tetrahydrofuran (5 mL) at room temperature and stir for 3 h. Dilute the mixture with ethyl acetate (20 mL) and wash with saturated sodium bicarbonate solution and brine (10 mL each), then dry the organic layer over sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (1:1), to provide the title compound as an off-white solid (0.297 g, 75%): 530 (M−H).

Workup

  1. washwash with saturated sodium bicarbonate solution and brine (10 mL each)
  2. dry with materialdry the organic layer over sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. customPurify the residue
  6. washeluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c923d3bd4283456c8f51531d75456eed
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07749992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes